AFCDB: Acetovanillone (FDB012055)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:58 UTC

Update date

2019-11-26 03:06:05 UTC

Primary ID

FDB012055

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetovanillone

Description

Acetovanillone, also known as 4'-hydroxy-3'-methoxyacetophenone or acetoguaiacon, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Acetovanillone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Acetovanillone is a faint, sweet, and vanillin tasting compound found in corn and garden onion, which makes acetovanillone a potential biomarker for the consumption of these food products. Acetovanillone may be a unique S.cerevisiae (yeast) metabolite.

CAS Number

498-02-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.04 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.07	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.9 m³·mol⁻¹	ChemAxon
Polarizability	16.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H10O3

IUPAC name

1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

InChI Identifier

InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

InChI Key

DFYRUELUNQRZTB-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=CC(=C1)C(C)=O

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

Classification

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyphenol
Acetophenone
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Anisole
Phenol ether
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:2781 )
aromatic ketone (CHEBI:2781 )
acetophenones (CHEBI:2781 )
Flavans, Flavanols and Leucoanthocyanidins (C11380 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.05%; H 6.07%; O 28.88%	DFC
Melting Point	Mp 115°	DFC
Boiling Point	Bp17.5 233° (lit. gives a pressure range)	DFC
Experimental Water Solubility	5 mg/mL at 20 oC	BEILSTEIN
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udi-4900000000-17a85dc123d088c3aa49	2015-03-01	View Spectrum
Predicted GC-MS	Acetovanillone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-2900000000-c2b9fc9aff1c67a83c67	Spectrum
Predicted GC-MS	Acetovanillone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetovanillone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetovanillone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-498ed957aa15729fb0a4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-c1c53a9c0ce83907c31f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-4900000000-9523f4aee91ded7398fa	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-dd966d68c334c4588c5a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-f50acbb85458094718fb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mn-5900000000-38c38f7aec7f03fc4aa6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5dea0e2df5cd18252bf0	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066s-0900000000-4aa899ac7457495c236b	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-488dceb176525121ae13	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9300000000-a7b7fde927bc2ff25c6e	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-fa257fa9b73b26e921ad	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-9160fcb70adace18630c	2021-10-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C11380

Pubchem Compound ID

2214

Pubchem Substance ID

Not Available

ChEBI ID

2781

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BJQ72-S:HCV60-D

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00002689

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

498-02-2

GoodScent ID

rw1057511

SuperScent ID

2214

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
NADPH-oxidase inhibitor	50423	An EC 1.6.3.* (oxidoreductase acting on NADH or NADPH with oxygen as acceptor) inhibitor that interferes with the action of NAD(P)H oxidase (H2O2-forming), EC 1.6.3.1.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
vanilla	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanillin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Acetovanillone (FDB012055)

Structure for FDB012055 (Acetovanillone)